4-Methylmorpholine → HCID 20825553, compound

Participants

Reaction Steps

To a stirred solution of 2-tert-butoxycarbonylamino-4,4-dimethyl-pentanoic acid (5 g, 20.3 mmol) and N-methyl morpholine (4.46 mL, 40.6 mmol) in THF (40 mL) at 0° C. was added isobutyl chloroformate (2.64 mL, 20.3 mmol) and, after 10 min, the solution of 1-amino-cyclopentanecarbonitrile (3.35 g, 30.5 mmol) in THF (40 mL). The mixture was allowed to warm to room temperature and stirred overnight. It was diluted with water, extracted with dichloromethane, washed with brine, dried (sodium sulfate) and concentrated to give the crude product. Chromatography on silica gel (dichloromethane:MeOH=30:1) gave [1-(1-cyano-cyclopentylcarbamoyl)-3,3-dimethyl-butyl]-carbamic acid tert-butyl ester (6.15 g, 89.6%).

Provenance & Evidence